2-chloro-5-methoxy-4-nitro-N-phenyl-benzamide → 4-amino-2-chloro-5-methoxy-N-phenyl-benzamide

HRID 1773503Notes

Reaction equation

HRID 1773503 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([O:20][CH3:21])=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]>C(OCC)(=O)C.N1C=CC=CC=1.O>[NH2:17][C:15]1[C:14]([O:20][CH3:21])=[CH:13][C:3]([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:5])=[C:2]([Cl:1])[CH:16]=1

Participants

4

Reactant 1

HCID 666645802-chloro-5-methoxy-4-nitro-N-phenyl-benzamide

Product 1

HCID 666646904-amino-2-chloro-5-methoxy-N-phenyl-benzamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 66926435Pyridine waterSolvent

Procedure

Stannous chloride (334 mg, 1.76 mmol) was added to a solution of 2-chloro-5-methoxy-4-nitro-N-phenyl-benzamide (180 mg, 0.59 mmol) in a mixture of ethyl acetate and ethanol (1/1, 8 mL) and the reaction mixture was stirred at room temperature overnight. The resulting mixture was partitioned between ethyl acetate (50 mL) and an aqueous solution of potassium carbonate (5%, 30 mL); the organic layer was separated, washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and evaporate under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 70/30) to give 82 mf of 4-amino-2-chloro-5-methoxy-N-phenyl-benzamide as an off-white solid.

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate (50 mL)
  2. customthe organic layer was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporate under reduced pressure
  7. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 70/30)

Sources & evidence

ORD record
ord-0b5ce07b1dea4a4787ed953f03afc191
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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